DE1492070A1 - Preparations for the cosmetic coloring of hair - Google Patents

Description

PATtNiANWALTE

PROF. PR DR J Fig ITS Γ ΟΤΓ F- "R Dli.-IM« ;. WOLFRAM ÜÜNTF

: ■ Ml'Ni ti :. :. HA i.sTKASSf Γ FLKNiItIf '.HlI

H92070

P 14 92 o7o. 8 Company L ¹ ORSAL

Munich, November 18, 1968 M / 7469

Preparations for the cosmetic coloring of hair

The invention relates to a cosmetic dyeing agent of hair. It consists in the fact that one or more antraquinone dyes the general formula

0 MH,

NHZ

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. Documents (* «. / 11 Abe. * Νγ. Ι

in which Z either -

or

means iV or their quartering

products, where in the latter case Z in the formula is as follows Importance is:

, R

- < ^cH ₂ > _n -

_| jt

CH ₂ - CH - N (O

ⁿ I ^N CH CH ^y

\ _Rm ^CH 2 - ^CH 2

CH ₀ - CH ₀ / ²
\ ² \
CH ₂ . ^CH 2 -CH ₂

- NO"

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η is an integer between 2 and 6 and R and R ¹ mean the same or different lower alkyl radicals, such as CH ₃ * ^C 2 ^H 5 or the like, or components of a heterocyclic radical, such as a morpholine or piperidine radical can.

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in which formulas η, R and R ^{1 have} the above meaning, while R ″ represents a lower alkyl radical or benzyl radical and A represents an anion, for example halogen, methosulfate or the like -Oiamino-5-nitro-anthraquinone either an N, N-dialkyl-alkylenediamine of the formula

R.
NH ₂ - (CH ₂ J _n - N ^

or a p- (N, N-dialkyl) phenylenediamine of the formula

expediently allowed to act at an elevated temperature. In these formulas, n, R and K ^{1 have} the meaning already given above.

The quaternization of the tertiary derivatives thus obtained is made with the help of a quarternizing agent such as dimethyl sulfate or an alkyl halide, optionally carried out in the presence of suitable solvents.

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The dyes mentioned below can also be obtained in this way.

1,4-diamino-5- M '"- (NrN-diethylamino) -propylaminoj -anthraquinone 1,4-diamino-5- (ß-morphoiino-ethylamino) -anthraquinone 1,4-diamino-5- ( f " - piperidino-propylamino) -anthraquinone

- (1,4-Diamino-anthraquinonyl-5-aininopropyl) - ί ^ - (N-methylpiper idinium) J methyl sulfate

1,4-Diaraino-5 ~ f p- (NN-dimethylamino) -phenyL-amino J - »- anthraquinone

px - (l _# 4-diamino-anthraquinonyl-5-aminopropyL) - ι '- (NN-diethyl-N-methylammonium) j -methyl sulfate

Γ -χ'- (1,4-Diaraino-anthraquinonyl-5-aminoethyl) -fl- (N-methylmorpholiniumjj methyl sulfate

[pi - (1,4-Diaraino-anthraquinonyl-5-aminopropyl) - ί ^ - (N-benzylpiperidinum) J -chloride

Γ 1,4-diaminoanthraquinonyl-5-aminophenyl-p- (N.N.N-trimethylaramonium) j -methyl sulfate.

In the case of cosmetic dyeing, the procedure is essentially that the dye solutions are kept for a sufficiently long time, e.g. 2o up to 30 minutes, keeps it in contact with the hair and then rinses, washes and dries it.

The new colorants have the advantage that they are within a very wide pH range, which can range from 3 to 9,

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“In particular, they are against the influences of the weather more resistant than the known dyes.

are soluble in water so that they meet all of the conditions found in the practice of hair coloring.

They are very resistant to sunlight and have a great affinity for keratin fibers, especially living ones Hair. "The new colorants are also well tolerated with the cosmetically common additives, such as penetrants, Swelling agents and the like.

The anthraquinone dyes to be used according to the invention can also be used with dyes that do not belong to this series, be used. They generally result in senr on the hair strong, animal blue color nuances and complement in particular fortunately the "range of those nuances, which with the help of other anthraquinone dyes, also from the applicant can be obtained.

The cosmetic hair dyes can be prepared by adding one or more of the above Dyes corresponding to the formula, optionally dissolving in water together with other dyes, and the desired Additives such as dispersants, plasticizers, odorants etc. admits. The concentration of the dyes can be

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BATH

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• f

vary within wide limits due to the high solubility; their choice is practically based on the desired result.

The hair is preferably colored at room temperature; the staining solution is used for a required period of time left to act on the hair "without it being necessary" to add an oxidizing agent to the solution.

In the following examples, the preparation according to the invention the dyes and their use are explained in more detail, but without being limited thereto.

example 1

Prepare a staining solution of the following composition: / \ - (l ^ -Diaminoanthraquinonyl-S-aminopropyD-l "-

- (N.N ^ diethyl-N-methylammonium) J -methyl sulfate Ig

Sodium carbonate up to a pH of 8

fill up with water to 100 cm

This solution is applied to up to 100 % white hair and left to act for 20 minutes at room temperature. Then you rinse with water, wash with a shampoo, rinse again and dry your hair. A strong blue color is obtained.

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Example 2

Prepare a staining solution of the following composition:

ino-S- (i ^ -piperidino-propylamino) -anthraquinone .... 0.5 g

Lactic acid up to a pH of

Fill up with water on loocm

This solution is applied to up to 100 % white hair and left on for 20 minutes at room temperature. This is followed by rinsing with water, washing with a shampoo, rinsing again and drying the hair. A greenish-blue coloration is obtained.

Prepare a staining solution of the following composition:

^ J. ^ Diaminoanthraquinonyl-5- f ^ aminophenylp- (N.N.N-triraethylamonionOJl. methyl sulfate 1 g

Sodium carbonate up to a pH of 7

Fill up with water to - loo cm

This solution is applied to up to 100% white hair and left on for 20 minutes at room temperature. Then you rinse your hair with water, wash with a shampoo, rinse again and finally dry. A "nattier" blue coloration is obtained.

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Beiggiel 4

The following solution is created:

ΓίΧ - (l ^ -Diarainoanthraquinonyl-S-arainopropyl) -f * ■ *

- (N.N-diethyl-N-methylararaoniura) j -methyl sulfate 0.5 g

[_iX - (4-Hydroxyanthraquinonyl-1-aminopropyl) - \ ¹ ^ -

- (N-methyl-piperidinium) -methyl sulfate 0.5 g

[U - (Anthraquinonyl-a-aminoäthyD-a- (NN-rdiethyl-

N-raethy! Ammonium) I -methyl sulfate 1.5 g

Sodium carbonate solution up to a pH of ......... 8.5

3 Fill up with water to 100 cm

This solution is applied to up to 90 % white hair and left on for 15 minutes, then rinsed with plenty of water and dried. The hair is colored gray.

The following solution is created:

- (1. ^ - Diaminoanthraquinonyl-S-arainopropyl) - ^ ^v - - (N-methyl-piperidinium) J -methyl sulfate 0.5 g

- (4-Hydroxyanthraquinonyl-1-aminopropyl) -r ^A "- - (N-methyl-piperidiniuraf] -methyl sulfate 0.5 g

- (Anthraquinonyl-2-aminoethyl) -ß- (N.N-.diethyl-N-methylammoniumH methyl sulfate 1 g

- {Anthrächinony1-1.5 bis aminoethyl-Γ SS (N-methyl-morpholinura) l \ -bis-methyl sulfate 0.2 g

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Sodium carbonate solution up to a pH of 7

Fill up with water on loocm

This solution is applied to up to 90 % white hair. After an exposure time of 15 minutes at room temperature, it is partially rinsed with water and dried. A brown coloration with ash-colored reflections is obtained.

Example 6

The following dye mixture is produced:

p-tolylenediamine. * 2 g

m-diamino anisole sulfate 0.2 g

Resorcinol 2 g

m-aminophenol 1 * 5 g

p-aminophenol 1 * 5 g

Jo ^ - (1.4-Diaminoanthraquinony 1-5-aminopropyI) -S-

- (N.N-diethyl-N-methylairanoniumT} -methyl sulfate 6 g

Ethylenediamino-tetraacetic acid 2 g

Ammonium thioglycolate 2 g

Ammonia, 2o% strength 7o g

Fill up with water to 100 cm

3 3

50 cm of this mixture is diluted with 50 cm of hydrogen peroxide (20% by volume) and applied to up to 90 % white hair. After 30 minutes of exposure, the hair is washed, rinsed and dried. An ash-blonde coloration is obtained.

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The embodiments of the invention explained in the examples are not intended to have a restrictive character and any changes can be made without the To leave the scope of the invention.

The following is noted in relation to the prior art. The implementation of l ^ -Diaraino-S-nitroanthraquinone with l-dimethylamino-3-aminopropane, l-dimethylamino-2-aminoethane, l-diethylamino-3-aminopropane, l-diethylamino-4-araino-n-pentane or N- (β-aminoethyl) piperidine is known, including the implementation the dyes obtained with dimethyl sulfate, diethyl sulfate, ToliAolsulfonsäure-methyl ester or benzyl chloride to the corresponding quaternized dyes.

It is also known that alkylaminoanthraquinones Alkyl radical carry tertiary amino groups or quaternary ammonium groups, already for dyeing wool or silk, i.e. that is, from keratin fibers.

It should be said that in these general statements only is carried out that alkylaminoanthraquinones with a tertiary amino group and a quaternary ammonium group par excellence already for dyeing wool or silk, i.e. has proposed textile keratin fibers, since, however, the dyes in question are derived from the textile keratin

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Allow fibers to be washed out easily and are therefore unsuitable for dyeing. In addition, one can speak of the färberextechnxschen Behavior of a coloring agent in the text-xlsektxor no conclusions on the dyerex-technical behavior in the cosmetic Close sector. Also one can know about the use of colorants in the cosmetic sector due to chemical Constitution does not make any reasonable predictions.

212 / v. 909887/1569

Claims (4)

Claims 1. Cosmetic coloring agent containing anthraquinone dyes, characterized in that «these of the constitutional formula MHZ in which Z either - (CH ₂ ) η - or means Yh between their quartering R * products correspond to »where in the latter case Z in the formula has the following meaning: 909887/1569 V 4, I / I \ * +) η is an integer between 2 and 6 and R and R ^{1 are} identical or different lower alkyl radicals, such as CH ₃ , ^C 2 ^H 5 or the like, or also components of a heteroxyclic radical, such as a morpholine or Pxperxdxnrestes, could be. 909887/1569 - CH < ^CH 2>"- (CH ₂ ) - I ^{2 n} i - CH CH CH ₂ - CH ₂ R " in which formulas n _f R and R * have the above meaning «while R » is a lower alkyl radical or benzyl radical and A is an anion », for example halogen, methosulphate or the like. 2. Colorant according to claim 1, characterized in that there are also other known dyes that can be used for the same purpose and, if necessary, other customary ones Additives such as dispersants, plasticizers, penetrants, Contains fragrances or the like. 9-0988 7/1 5 6S - ¹ W- 41 * 3. Coloring agent according to claims 1 and 2 »characterized» daft ee has a pH of 3 to 9. 4. Cosmetic dyeing process using dyes according to Claims 1 to 3, characterized in that that the fibers or hair to be dyed are impregnated with such an agent and allowed to act for 15 to 60 minutes, preferably at room temperature, then rinsed with water and then with a detergent washes »again rinses and dries. 909887/1 569